Are Kris Jenner and Ben Flajnik Dating? A Timeline of Everything We Know

Talk that the 58-year-old Kardashian matriarch and the 31-year-old former Bachelor star were dating started back in late September, but has been all over the headlines on the morning of November 26. The Us Weekly December 9 print edition features a cover story on the pair, with multiple sources saying they’re hooking up. Ben immediately denied it in a tweet, writing, “Here we go again. Hey@usweekly maybe put a call into me once and a while for some fact checking. Sincerely,#TheTruth.”

The Bachelor also spoke to People.com to set the record straight. “She's a beautiful, smart woman. But we're friends,” he said in an exclusive. Kris, too, was quick to deny the story. "Ben and I are good friends," she told E! Online in an exclusive statement. "I think he is a great guy but we aren't dating!”

First Glance

Back in late September, Kris posted a pic of them and family friend Jonathan Cheban in Sonoma. Ben owns a vineyard called Envolve, and it was later said that Kris headed to wine country to film a segment of Keeping Up With the Kardashians.

A little over a week later, on October 8, Kris and Bruce Jenner, her husband of 22 years, announced that they were getting separated, spurring a whole new round of rumors. On October 10, InTouch picked up a story from a source who said that Kris “has a crush” on the Season 16 Bachelor, and that they have “been spending a lot of time together.”

Ben Denies It, Volume 1

Ben went immediately to Us Weekly at the time, trying to set the record straight. "I did Kris' talk show a few months back, brought my wines on the show. Of course I offered her a visit to the winery whenever she had a chance," Ben explained to Us.

"That's how we met. Recently, she ended up contacting me about a month ago or so and asked me if they could film an episode of Keeping Up With the Kardashians at the winery. I of course obliged." He went on to say that he’s been dating a girl who is local and in the wine business, and had been for a few months.

Out on the Town

Sometime around Ben’s September 10 birthday, the pair also traveled to Mexico to hang with mutual friend Girls Gone Wild creator Joe Francis and some friends.

Then, on October 23, Kris and Ben both Instagrammed photos at the Kanye West concert, tagging each other in the captions, though neither posted shots together. Two days later, Kris went off to Las Vegas for daughter Kim Kardashian’s birthday, and Ben was spotted driving her white Bentley in Huntington Beach.

Projects, Ya Know

“Ben was telling people that Kris said he could use the car for the weekend,” an anonymous sources told Us Weekly in the December 9 print edition of the magazine. Two days after that, People.com ran a story about their rumored relationship, and again Ben denied that anything was happening.

“Kris is a very dear friend of mine. We are not dating, we’re just working on a couple of projects together, so that’s why we’ve been seen a lot as of late,” he told the site.

Wetpaint Entertainment caught up with the Bachelor around the same time. “She’s amazing,” he told us, adding that one of the projects is “potentially in television.” He added that he’s met Kim and baby North West, but not the rest of the girls, and probably wouldn’t be invited to the Kimye wedding of the century.

The Age Difference

As for whether this whole 27-year difference would even happen in Kris’s busy world, we’re not sure. The mom of six did tell ET Online in mid-November that she wouldn’t rule out a new relationship in the midst of all her split drama with Bruce — and that she doesn’t mind dating someone who isn’t her age. “You find who you fall in love with in life. If they happen to be a certain age, they happen to be a certain age.”

November 26: The Fan Has Been Hit

In the December 9 print edition of Us Weekly, which was made available on November 26, the cover story headline read, “Bachelor Playboy Secret Affair! Life after Bruce! Kris has a wild fling with bad boy Ben Flajnik. What her family really thinks.”

In the story, sources said he had met all her kids and they “love him,” adding that though they’re “hanging out.” The sources also say they’re “not exclusive; it’s more casual” and that the whole thing started because she pursued him. Besides the October Kanye show in Cali, sources said Kris also took Ben to others, has been “taking him everywhere and paying for everything” and has been a “total sugar mama.”

As for where Ben’s coming from, these all-knowing anonymous sources have said that he “always had a thing for rich older ladies.” One supposed friend of Ben also mentioned that they’re planning another vacation for December.

Deny, Deny, Deny

Ben doesn’t seem to be on quite the same page as all his “friends” who are talking to tabloids, though. He immediately went to People.com to set the record straight. As for why he was driving Kris’s Bentley, he says she just let him borrow it, because he didn’t have one. You know, like friends do.

"It is like you can't do anything without people thinking you're hooking up or in a relationship,” he says of going to Mexico with his friends, including Kris. The site also added that Ben is currently single, making us wonder what happened to the girl he mentioned just a few weeks ago.

And Ben has been in contact with Kris, saying in the People.com interview, “We talked this morning and she said, 'Hey, don't worry.' She understands why I'm upset and uncomfortable with [the reports.] She deals with this kind of thing on a daily basis, and I've worked really hard to stay away from this kind of image."

As mentioned, Ben also tweeted about his feelings, and Kris spoke to E! Online, both saying that nothing is happening between them but a beautiful friendship. Beyond that, we’re not sure what else they can say.

You got all that? What do you think: Are they or aren’t they? React in our poll and then share your thoughts below!